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Make smart choices about your money, time and productivity

Oct 16, 2017

#99: Thirteen years ago, Joshua Dorkin's friends teased him about starting a website that seemed to have no future.

"I would get calls from my buddies who would literally call me on my cell phone [and say] 'Hey Josh, we just walked past a penny on the ground. We were thinking about picking it up and mailing it to you."

At the time, Dorkin had just launched BiggerPockets, a then-nascent website about real estate investing.

"I was working a full-time job making no money as a teacher," Dorkin says, "... and then [I] quit that job, reliable income, to blindly create this platform for other people. And I was helping other people get rich, and I was broke."

Dorkin spent the next 8 years working mostly as a one-man operation as he tried to monetize a fledgling website.

"We were struggling and scrapping by on every AdSense check that we could collect," Dorkin says. "The business really wasn't making serious money for probably getting close to a decade."

The story has a happy ending. Today, BiggerPockets has grown to more than 870,000 members. The podcast has almost 250 episodes and the blog features more than 8,100 articles.

In today's episode, I have a heart-to-heart with BiggerPockets founder Joshua Dorkin about the blood, sweat and tears that's required to start a successful online business. What lessons did he learn along the way? What regrets does he hold? And what advice would he share with other aspiring online entrepreneurs?

We don't talk about real estate investing in today's episode. Instead, Joshua and I focus on the harsh realities of growing an digital empire.



You can find more information in the show notes at